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Volumn 133, Issue 9, 2011, Pages 3208-3216

Total synthesis of brevenal

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND; CONVERGENT SYNTHETIC STRATEGY; CYCLIZATION REACTIONS; TOTAL SYNTHESIS;

EID: 79952259432     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200089f     Document Type: Article
Times cited : (44)

References (80)
  • 1
    • 77954798010 scopus 로고    scopus 로고
    • For reviews on the synthesis of ladder toxins, see: Isobe, M.; Hamajima, A. Nat. Prod. Rep. 2010, 27, 1204-1226
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 1204-1226
    • Isobe, M.1    Hamajima, A.2
  • 4
    • 30744459350 scopus 로고    scopus 로고
    • Nakata, T. Chem. Rev. 2005, 105, 4314-4347
    • (2005) Chem. Rev. , vol.105 , pp. 4314-4347
    • Nakata, T.1
  • 6
    • 61549121088 scopus 로고    scopus 로고
    • For reviews on the impact of red tides and ciguatera on the environment and human health, see: Landsberg, J. H.; Flewelling, L. J.; Naar, J. Harmful Algae 2009, 8, 598-607
    • (2009) Harmful Algae , vol.8 , pp. 598-607
    • Landsberg, J.H.1    Flewelling, L.J.2    Naar, J.3
  • 7
    • 33750949790 scopus 로고    scopus 로고
    • Lewis, R. J. Toxicon 2006, 48, 799-809
    • (2006) Toxicon , vol.48 , pp. 799-809
    • Lewis, R.J.1
  • 18
    • 34250845081 scopus 로고    scopus 로고
    • Potera, C. Science 2007, 316, 1561-1562
    • (2007) Science , vol.316 , pp. 1561-1562
    • Potera, C.1
  • 36
    • 79952257570 scopus 로고    scopus 로고
    • We employed a related strategy in our synthesis of gambierol. See refs 10a and 10b
    • We employed a related strategy in our synthesis of gambierol. See refs 10a and 10b.
  • 39
    • 79952263628 scopus 로고    scopus 로고
    • Nicolaou showed that the Tebbe reagent performs OLEC reactions via an enol ether-olefin RCM reaction. See ref 17
    • Nicolaou showed that the Tebbe reagent performs OLEC reactions via an enol ether-olefin RCM reaction. See ref 17.
  • 45
    • 79952258032 scopus 로고    scopus 로고
    • 2, MeMgBr). Alternate substrates have included the use of TBS ethers, benzyl ethers, and cyclic acetals instead of the dimethyl acetal in 14.
    • 2, MeMgBr). Alternate substrates have included the use of TBS ethers, benzyl ethers, and cyclic acetals instead of the dimethyl acetal in 14.
  • 48
    • 79952271325 scopus 로고    scopus 로고
    • We believe that the facial selectivity in the epoxidation of 18 is dictated by the C(12) angular methyl group and that the C(16) stereochemistry comes from the direct opening of the epoxide with allyl magnesium bromide. See ref 25
    • We believe that the facial selectivity in the epoxidation of 18 is dictated by the C(12) angular methyl group and that the C(16) stereochemistry comes from the direct opening of the epoxide with allyl magnesium bromide. See ref 25.
  • 52
    • 79952268864 scopus 로고    scopus 로고
    • See ref 34
    • See ref 34.
  • 53
    • 29044439970 scopus 로고    scopus 로고
    • The use of additives to overcome olefin isomerization has largely been unsuccessful in our hands. For examples of the successful inhibition of olefin isomerization during RCM, see: Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 17160-17161
    • Hong, S.H.1    Sanders, D.P.2    Lee, C.W.3    Grubbs, R.H.4
  • 60
    • 79952254588 scopus 로고    scopus 로고
    • We speculate that the role of toluene is to stabilize the oxocarbenium intermediate through π-stacking interactions
    • We speculate that the role of toluene is to stabilize the oxocarbenium intermediate through π-stacking interactions.
  • 65
    • 79952262190 scopus 로고    scopus 로고
    • Wei has reported a similar phenomenon. See ref 38a
    • Wei has reported a similar phenomenon. See ref 38a.
  • 66
    • 79952269811 scopus 로고    scopus 로고
    • See refs 7a and 8
    • See refs 7a and 8.
  • 73
    • 79952258395 scopus 로고    scopus 로고
    • Ketone 46 was prepared in six steps from 42
    • Ketone 46 was prepared in six steps from 42.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.